With this New award, the Chemical Synthesis Program supports Professor Matthias Brewer of University of Vermont & State Agricultural College in a project investigating new chemical syntheses that will provide routes to a variety of structurally complex molecules. Several of these new transformations will follow unique routes that are not accessible by current synthetic methods. The new organic molecules that will be prepared will be of fundamental importance to researchers seeking to develop new pharmaceuticals and other molecules of biological interest. These studies will provide a mechanism for the training of developing scientists in the areas of synthetic organic chemistry, reaction design, total synthesis and complex structure elucidation. This project will also give a summer research experience to an economically disadvantaged high school student.
The project will investigate the intramolecular reactions of in situ-generated 1-aza-2-azoniaallene salts in the synthesis of nitrogen heterocycles. Aspects of these novel heteroallene salts that will be explored include C-H insertion reactions, reactions involving aziridinium ion intermediates, cycloaddition reactions and the use of this methodology for the total synthesis of (+)-ibophyllidine. This work will provide new ways to prepare structurally complex nitrogen heterocycles under mild, low temperature, conditions.
